[Cl-:1].[Cl:2][CH2:3][CH2:4][NH+:5]([CH2:15][CH2:16]Cl)[CH2:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][NH2:27])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[ClH:2].[ClH:1].[CH3:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][N:27]2[CH2:16][CH2:15][N:5]([CH2:6][CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:4][CH2:3]2)[CH:22]=[CH:23][CH:24]=1To the solution of bis(2-chloroethyl)-(3-phenylpropyl)ammonium chloride (1.78 g, 6 mmol) and 2-(3-methylphenyl)ethanamine (0.811 g, 6 mmol) in 8 mL of DMF is added anhydrous potassium carbonate (2.48 g, 18 mmol) and sodium iodide (1.80 g, 12 mmol) successively. The reaction mixture is then stirred at 80° C. for 4 hours and then cooled to ambient temperature. Water and ethyl acetate are then added to the resultant reaction mixture. The organic layer is separated, washed 3 times with water and once with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue is dissolved in ethanol. To this solution is added 6 N hydrochloric acid drop wise with cooling until pH 3. The resulting solution is maintained at 4° C. overnight. The resultant crystals are collected by filtration and washed with ether to give 97 mg of the title compound (5%).
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